This depends highly on what you're optimizing for in a job (read: what burned you before that you don't want to get burned by again)
Some questions for CEO/upper management that I intend to ask next time:
Tell me about the coolest thing you made without help from anybody else.
(This question is basically: "do you know what its like to make, not manage?" There are totally different mindsets and ways of measuring time and whatnot. I want a manager who has felt those themselves.)
Tell me about a time you let your team down, and how you got through it.
(This is somewhat of a trick question: can they admit that they've let their team down at some point? Can they blame themselves or fall back to other factors? Lots of important stuff comes out here)
How often do you say no to a feature or initiative even though it seems like it might be a good idea?
Some questions for CEO/upper management that I intend to ask next time:
Tell me about the coolest thing you made without help from anybody else.
(This question is basically: "do you know what its like to make, not manage?" There are totally different mindsets and ways of measuring time and whatnot. I want a manager who has felt those themselves.)
Tell me about a time you let your team down, and how you got through it.
(This is somewhat of a trick question: can they admit that they've let their team down at some point? Can they blame themselves or fall back to other factors? Lots of important stuff comes out here)
How often do you say no to a feature or initiative even though it seems like it might be a good idea?
(Can they say no and mean it? Cleanly? Huge.)